Hydrogen bonding, alkyl chain crystallization and constitutional isomerism in solid-state self-assembly of dodecyloxyisophthalic acid complexes

Abstract

Self-assembly of the molecular complexes of O-alkoxy isophthalic acid (5-C12 and 4-C12) with 4,4′-bipyridine (bipy) in the crystal lattice is described. Complexes 5-C12ISA·bipy and 4-C12ISA·bipy exhibit 3-D supramolecular structures through and interplay of H-bonding, alkyl chain interdigitation, π⋯π and C-H⋯π interactions. The former forms a unique triple helix which further assembles into a 2D network stabilized via π⋯π stacking interactions. The latter forms hydrogen bonded supramolecular sheets. © The Royal Society of Chemistry 2005.